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Vacation rentals in Middlesboro

Vacation rentals in Middlesboro

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlesboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Powell River Resort And Adventure’s ⭐️⭐️⭐️⭐️⭐️
    SUPERHOSTEntire cabin · 8 guests · 3 beds · 2 bathrooms
    Powell River Resort And Adventure’s ⭐️⭐️⭐️⭐️⭐️

    🐟🚣🏽‍♀️🚴‍♀️🥾 We offer kayaking, mountain biking, hiking, fishing and camping. Send me a message through this cabin listing to schedule your experiences through my personal calendar. WE TAKE ALL EXTRA PRECAUTIONS FOR AN EXTREMELY CLEANED AND SANITIZED CABIN BEFORE EACH AND EVERY ARRIVAL SO DON’T WORRY ABOUT A THING:) We offer a breathtaking mountain and river living experience. You’ll stay in a fully furnished log house with everything you need and then some.

    What guests are saying:

    “We found Richie's place after a late night decision to take off the next day for a mini COVID vacation with our 4 kids and furbaby. Richie's instructions to get to the cabin were spot on and everything was ready for a last minute booking. Off the beaten road and up a driveway that is well described in the listing. Our minivan made it up and down daily with no issues. The cabin was much larger than we expected. Very spacious and open with a rustic and personal decor that makes it feel so comfy! Everything you could need Richie had available. Plenty of extra sheets and blankets, air mattress, shampoo/body wash, books, board games, laundry soap, and the most important to me is a fully furnished kitchen with access to a pantry for those little things you hate to buy when traveling. (And more!) The Playstation is a PS3 if you would like to bring your own games. The bedrooms do not have TV's but it was a nice switch up for the kiddos to entertain themselves outdoors or doing something more productive TOGETHER. As Richie describes, it is very rustic. If your wanting the idea of cabin without the authenticity of a real cabin, this is not for you. The upstairs loft bedrooms stayed a little warm. Heat rises!! We went and bought a fan and it cooled it off enough the kids didn't complain. The large deck was a relaxing place to unwind once the kids were in bed. The river access is at the bottom across from the driveway entrance. Richie gave us the go ahead to shoot fireworks with the kiddos one evening on the riverfront and they had a blast! There is not much yard space by the cabin, so if you have a dog that is weird about were they use the restroom, you may need to walk the driveway a little bit. We had one concern upon arriving which Richie was kind and quick to accommodate us and resolve the issue. Richie is friendly, attentive, and cares about his guests experience. An awesome host that thinks of all the little things! My suggestions: If you get a chance, check out Heavy's BBQ and Frostee Drive In for some good food and Gap Creek Coffee House for the best coffee and cake ever! They had our business 3 days in a row. Take a day and visit the Gap. Walk around the quaint little Town. The Old Drugs Store is closed but you can read some interesting facts in the windows of the store. Actually of my family history! We also walked the train tracks. Visit Tri-State Peak and do not miss the Overlook! Thank you Richie for allowing us to stay in your home so that we could quarantine somewhere else, enjoy nature, and show our kids some of moms family history! Memories were made! 😊”

  • Guest house in the country with a beautiful view
    SUPERHOSTEntire house · 2 guests · 2 beds · 1 bathroom
    Guest house in the country with a beautiful view

    Located in a peaceful country setting with a beautiful view from the front porch. It is conveniently located near Lincoln Memorial University, Norris Lake, and Historic Cumberland Gap. We live next door to the guest house and will be there to greet you upon arrival to answer any questions you may have.

    What guests are saying:

    “We arrived after dark for our stay and were not only given clear instructions, but plenty of automatic lighting to make unpacking a breeze. We were tickled the moment we opened the door due to the personal and welcoming atmosphere. Amy put so many extra touches into ensuring a very welcoming and comfortable visit. The place was absolutely spotless and had every amenity you could possibly need. One of the most enjoyable home away from home experiences! If you’re in the area, this is the place to stay!”

  • Pirate Cove on Norris Lake. Lakefront
    SUPERHOSTEntire guest house · 4 guests · 3 beds · 1 bathroom
    Pirate Cove on Norris Lake. Lakefront

    Lakefront - This rental is the new addition to our home. It has its own private entrance, your private great room, Master ensuite with huge walk in shower. There is a Day bed with trundle in the great room that would be perfect for extra guest. This part of our home is separated from our own personal living space by a sliding barn door that will be latched for your privacy. Although we will be in the main part of the home we want you to enjoy your time and enjoy Norris Lake.

    What guests are saying:

    “As fellow AirBNB hosts, my husband and I tend to have pretty high standards when we are traveling as guests and our experience here surpassed all of our expectations! Lisa and Bruce are incredibly friendly and gracious hosts. We had less than perfect weather our first day and a half, so they generously let us arrange a late check out to enjoy more on our last day. The space is beautiful, spacious, and very clean. Having access to a grill and the kitchen was great, as we were able to cook meals in! The location is fabulous! Being able to walk down the yard and straight onto the dock and into the water was perfect! We didn’t have a boat or anything, but we did bring a two person float and just lounged within swimming distance of the dock and it was lovely. We brought our dog with us and she had a blast roaming all around the huge backyard and playing with their two dogs, Toby and Cooper. If you love dogs, this is the place for you! Their dogs are so sweet and friendly and just want to play fetch all day (which we didn’t mind at all). We will definitely return for another relaxing retreat to the lake!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Middlesboro holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Middlesboro

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement
SUPERHOSTEntire cottage
Scenic 1 BR Cabin w/ Hiking to Hensley Settlement
Price:£71 / night
The Inn over Angelo's
SUPERHOSTEntire guest suite
The Inn over Angelo's
Price:£79 / night
Home away from home
SUPERHOSTEntire house
Home away from home
Price:£70 / night
Room 2 within the Gambrel House
SUPERHOSTPrivate room
Room 2 within the Gambrel House
Price:£31 / night
Cozy Log Cabin in the woods, close to town.
Entire cabin
Cozy Log Cabin in the woods, close to town.
Price:£79 / night
The Little Dipper! Lake front w/private boat dock!
SUPERHOSTTiny house
The Little Dipper! Lake front w/private boat dock!
Price:£139 / night
BASE CAMP I next to Cumberland Gap National Park
Entire flat
BASE CAMP I next to Cumberland Gap National Park
Price:£71 / night
The Gregory Estate
SUPERHOSTPrivate room
The Gregory Estate
Price:£49 / night
Norris lakefront home with covered boat dock
SUPERHOSTEntire house
Norris lakefront home with covered boat dock
Price:£126 / night
Room 2 within Pine Mountain Bed & Breakfast
SUPERHOSTRoom in boutique hotel
Room 2 within Pine Mountain Bed & Breakfast
Price:£47 / night
Anchor Down Villa
SUPERHOSTEntire villa
Anchor Down Villa
Price:£118 / night
Norris Lake Water Haven (+optional pontoon rental)
SUPERHOSTHouseboat
Norris Lake Water Haven (+optional pontoon rental)
Price:£150 / night
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